Ask HN: Joining a startup right after fundraising?

I joined a startup shortly after a big raise and this is the basis for my comment. I have also been on an internal team that was (simplifying) speculative investment, meaning we got to try a lot of stuff without being immediately accountable for revenue. It's only two data points.

Pros are that exuberance is at a high point and it's a period of growth, investment, and optimism, so you will get to do all of the fun stuff and ignore the boring stuff (unless the company is really well run). Don't discount this - it's really cool to be able to try lots of new stuff without having to be under constant pressure. Even if management is more frugal than the places I was, it's a whole different thing to be somewhere during the belt tightening phase where reality sets in and positive results are due immediately. There is a rewarding career to be had jumping between places that are in growth mode.

Re options / equity, value them at zero unless you're senior leadership (unless I'm misunderstanding and there is a liquid market for the shares pre IPO or acquisition). My options were worthless, even in an acquisition. There are countless ways they can lose all value, and unless you're a key part of steering the company, consider them a lottery ticket, not part of total comp

Is the risk really highest right after fundraising? Theoretically they just got a huge infusion of cash, so you should be relatively confident that the money will allow the company to survive at least for a bit.

My understanding of equity grants is that you're entitled to a specific amount of shares. If that's the case, it's not worth deferring your employment. If I plan to sell the stock 2 years from now, it doesn't matter when I got the stock (as the price 2 years from now is unrelated to when specifically I receive my shares).